JPH082847B2 - 4-allyl-2,6-diethylaniline and process for producing the same - Google Patents
4-allyl-2,6-diethylaniline and process for producing the sameInfo
- Publication number
- JPH082847B2 JPH082847B2 JP10178088A JP10178088A JPH082847B2 JP H082847 B2 JPH082847 B2 JP H082847B2 JP 10178088 A JP10178088 A JP 10178088A JP 10178088 A JP10178088 A JP 10178088A JP H082847 B2 JPH082847 B2 JP H082847B2
- Authority
- JP
- Japan
- Prior art keywords
- allyl
- diethylaniline
- present
- producing
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、医薬、農薬等の製造中間体として有用な新
規な４−アリル−2,6−ジエチルアニリン及びその製造
法に関する。TECHNICAL FIELD The present invention relates to a novel 4-allyl-2,6-diethylaniline useful as an intermediate for producing pharmaceuticals, agricultural chemicals and the like, and a production method thereof.
本発明化合物は、特に除草活性を有するピロン−３−
カルボキサミド化合物（特願昭62−164393）の製造中間
体として有用である。The compound of the present invention is particularly a pyrone-3- having herbicidal activity.
It is useful as a production intermediate for carboxamide compounds (Japanese Patent Application No. 62-164393).
（従来技術および発明が解決しようとする課題） 本発明化合物は、本発明者らによって初めて合成され
た新規化合物である。本発明者らは、除草活性を有する
ピロン−３−カルボキサミド化合物の製造法について検
討した結果、本発明化合物がその製造中間体として重要
であることおよびこの有利な製造法を見い出し本発明に
至った。(Prior Art and Problems to be Solved by the Invention) The compound of the present invention is a novel compound synthesized by the present inventors for the first time. The present inventors have studied the method for producing a pyrone-3-carboxamide compound having herbicidal activity, and as a result, have found that the compound of the present invention is important as a production intermediate thereof and have found this advantageous production method, and have reached the present invention. .
（課題を解決するための手段） 本発明は、４−アリル−2,6−ジエチルアニリン及び
その製造法に関する。(Means for Solving the Problems) The present invention relates to 4-allyl-2,6-diethylaniline and a method for producing the same.
本発明化合物である４−アリル−2,6−ジエチルアニ
リンは、Ｎ−アリル−2,6−ジエチルアニリンを酸と共
に、又は、Ｎ−アリル−2,6−ジエチルアニリンの酸付
加塩を加熱処理することによって製造することができ
る。The compound of the present invention, 4-allyl-2,6-diethylaniline, is obtained by heat treating N-allyl-2,6-diethylaniline with an acid or an acid addition salt of N-allyl-2,6-diethylaniline. Can be manufactured.
原料のＮ−アリル−2,6−ジエチルアニリンは、2,6−
ジエチルアニリンとアリルハライドを反応させることに
よって得ることができる。アリルハライドとしては、塩
化アリル、臭化アリル又は、ヨウ化アリルが挙げられ
る。The starting material, N-allyl-2,6-diethylaniline, is 2,6-
It can be obtained by reacting diethylaniline with allyl halide. Examples of the allyl halide include allyl chloride, allyl bromide, and allyl iodide.
反応に用いる酸としては、塩酸、臭化水素、硫酸、硝
酸、リン酸などの鉱酸の他、塩化亜鉛、塩化アルミニウ
ム、塩化第二鉄、四塩化チタン、BF3などのルイス酸が
挙げられる。又、酸付加塩としては、Ｎ−アリル−2,6
−ジエチルアニリンの塩酸塩、臭化水素酸塩、硫酸塩、
硝酸塩、リン酸塩などが挙げられる。Examples of the acid used in the reaction include mineral acids such as hydrochloric acid, hydrogen bromide, sulfuric acid, nitric acid and phosphoric acid, and Lewis acids such as zinc chloride, aluminum chloride, ferric chloride, titanium tetrachloride and BF 3. . Moreover, as an acid addition salt, N-allyl-2,6
-Diethylaniline hydrochloride, hydrobromide, sulfate,
Examples thereof include nitrates and phosphates.
加熱処理する際の温度としては、80℃以上が好まし
い。The temperature for the heat treatment is preferably 80 ° C. or higher.
この反応は、無溶媒下で行うことができるが、例え
ば、ベンゼン、トルエン、キシレン、メシチレン等の不
活性溶媒を用いてもよい。This reaction can be performed in the absence of a solvent, but an inert solvent such as benzene, toluene, xylene, mesitylene may be used.
尚、原料のＮ−アリル−2,6−ジエチルアニリンは、
単離したものを用いる必要はなく、2,6−ジエチルアニ
リンとアリルハライドとを反応させた後、単離精製する
ことなく利用することができる。The raw material N-allyl-2,6-diethylaniline is
It is not necessary to use the isolated product, and it can be used without isolation and purification after reacting 2,6-diethylaniline with allyl halide.
本発明化合物の精製方法は、特に限定されるものでは
ない。一般には、中和処理、抽出、蒸留、カラムクロマ
トグラフィー等によって精製することができる。The method for purifying the compound of the present invention is not particularly limited. Generally, it can be purified by neutralization treatment, extraction, distillation, column chromatography and the like.
さらに、本発明化合物は、ｐ−アリルアニリンをルイ
ス酸触媒の存在下、エチレンを加圧下に作用させること
によっても得ることができる。この場合、ルイス酸触媒
として、無水塩化アルミニウムが好適に用いられる。Furthermore, the compound of the present invention can be obtained by reacting p-allylaniline with ethylene under pressure in the presence of a Lewis acid catalyst. In this case, anhydrous aluminum chloride is preferably used as the Lewis acid catalyst.
尚、本発明の製造法によって得られる本発明化合物４
−アリル−2,6−ジエチルアニリンから、例えば、下記
ルートによって一般式（Ｉ）で示される除草活性を有す
る化合物が得られる。The compound 4 of the present invention obtained by the production method of the present invention
From allyl-2,6-diethylaniline, for example, the compound having the herbicidal activity represented by the general formula (I) can be obtained by the following route.
（R1,R2,R3は低級アルキル基を示す） 以下に実施例を挙げて本発明をさらに詳しく説明す
る。 (R 1 , R 2 and R 3 represent a lower alkyl group) The present invention is described in more detail below with reference to Examples.
（実施例） 2,6−ジエチルアニリン74.5g及び塩化アリル19.1gの
混合物を100℃で23.5時間加熱した。室温まで冷却した
後、水酸化ナトリウム水溶液でアルカリ性とした後、ト
ルエン抽出した。有機層を無水硫酸マグネシウムで乾燥
後脱溶媒した。残さにキシレン200ml加え、ディーンス
ターク装置を用いて、乾燥した後、塩化亜鉛70.9gを加
え、100℃で３時間加熱した。反応混合物を冷却した
後、水酸化ナトリウム（150g）の水溶液500mlを加え、
エーテル抽出した。有機層を無水硫酸マグネシウムで乾
燥後、濃縮し、残さを蒸留して、４−アリル−2,6−ジ
エチルアニリンを27.9g得た（bp125−126℃/0.9mmH
g）。1H NMR（CDCl3）δ1.24（6H,t）,2.64（4H,q）,3.
27（2H,d）,3.50（2H,br）,4.80−5.25（2H,m）,5.50−
6.30（1H,m）,6.73（2H,s）。(Example) A mixture of 74.5 g of 2,6-diethylaniline and 19.1 g of allyl chloride was heated at 100 ° C for 23.5 hours. After cooling to room temperature, the mixture was made alkaline with an aqueous sodium hydroxide solution and extracted with toluene. The organic layer was dried over anhydrous magnesium sulfate and then desolvated. To the residue, 200 ml of xylene was added, dried using a Dean Stark apparatus, 70.9 g of zinc chloride was added, and the mixture was heated at 100 ° C. for 3 hours. After cooling the reaction mixture, 500 ml of an aqueous solution of sodium hydroxide (150 g) was added,
It was extracted with ether. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the residue was distilled to obtain 2-allyl-2,6-diethylaniline (27.9 g, bp 125-126 ° C / 0.9 mmH).
g). 1 H NMR (CDCl 3 ) δ 1.24 (6H, t), 2.64 (4H, q), 3.
27 (2H, d), 3.50 (2H, br), 4.80−5.25 (2H, m), 5.50−
6.30 (1H, m), 6.73 (2H, s).
Claims (3)
の存在下で加熱処理することを特徴とする４−アリル−
2,6−ジエチルアニリンの製造法。2. N-allyl-2,6-diethylaniline is heat-treated in the presence of an acid, 4-allyl-
A method for producing 2,6-diethylaniline.
付加塩を加熱処理することを特徴とする４−アリル−2,
6−ジエチルアニリンの製造法。3. 4-Allyl-2, which is characterized in that an acid addition salt of N-allyl-2,6-diethylaniline is heat-treated.
Method for producing 6-diethylaniline.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10178088A JPH082847B2 (en) | 1988-04-25 | 1988-04-25 | 4-allyl-2,6-diethylaniline and process for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10178088A JPH082847B2 (en) | 1988-04-25 | 1988-04-25 | 4-allyl-2,6-diethylaniline and process for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01272556A JPH01272556A (en) | 1989-10-31 |
| JPH082847B2 true JPH082847B2 (en) | 1996-01-17 |
Family
ID=14309707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10178088A Expired - Lifetime JPH082847B2 (en) | 1988-04-25 | 1988-04-25 | 4-allyl-2,6-diethylaniline and process for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH082847B2 (en) |
-
1988
- 1988-04-25 JP JP10178088A patent/JPH082847B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01272556A (en) | 1989-10-31 |
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